CAS 57-22-7|vincristine|Vincrex|Vincristina [DCIT]|Vincristinum [INN-Latin]|VCR|Vincristine Sulfate PFS|Leurocristine|Vincrystine|Vincristine|Oncovin|22-Oxovincaleukoblastine|Vincasar|VIN|LCR|Indole...

General Information

Structure

Molecular Formula

C₄₆H₅₆N₄O₁₀

Molecular Mass

824.95764

Exact Mass

824.39964401

Charge

InChI

InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1

InChIKey

OGWKCGZFUXNPDA-XQKSVPLYSA-N

Canonic Smiles

O=CN1c2cc(OC)c(cc2[C@]23[C@@H]1[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@]1([C@@H]3N(CC2)CC=C1)CC)[C@]1(C[C@@H]2CN(CCc3c1[nH]c1c3cccc1)C[C@](C2)(O)CC)C(=O)OC

Isomeric Smiles

O([C@@H]1[C@]2([C@@H]3N(CC[C@@]43[C@@H](N(c3c4cc(c(OC)c3)[C@]3(C[C@H]4C[C@](O)(CN(C4)CCc4c3[nH]c3c4cccc3)CC)C(=O)OC)C=O)[C@@]1(O)C(=O)OC)CC=C2)CC)C(=O)C

Calculated Properties

JChem

Acid pKa

10.849017

H Acceptors

H Donor

LogD (pH = 5.5)

-2.3829613

LogD (pH = 7.4)

1.1448158

Log P

3.128179

Molar Refractivity

221.4804

Polarizability

87.836975

Polar Surface Area

171.17

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

3.36

LOG S

-4.44

Solubility (Water)

3.00e-02 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

vincristineVincristina [DCIT]Vincristinum [INN-Latin]VCRLeurocristineVincrystineVincristine22-OxovincaleukoblastineVINLCRIndole alkaloidZ-D-Val-Lys(Z)-OHVincristine SulfateVincrstine

Brand Name

VincrexVincristine Sulfate PFSOncovinVincasarVinkristinMarqiboVincasar PFSOnco TCS

IUPAC name

methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate

IUPAC Traditional name

sulfate, vincristine vincristine sulfate

Names and Identifiers

Registration numbers

PubChem SID

PubChem CID

CAS Number

Medline Plus

CHEBI ID

Wikipedia Title

Unique Ingredient Identifier

CHEMBL

KEGG ID

DrugBank ID

Chemspider ID

ATC CODE

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

2.8

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00541

Drug Groups

approved; investigational

Description

Antitumor alkaloid isolated from Vinca Rosea. (Merck, 11th ed.)

Indication

For treatment of acute leukaemia, malignant lymphoma, Hodgkin's disease, acute erythraemia, acute panmyelosis

Pharmacology

Vincristine is a vinca alkaloid antineoplastic agent used as a treatment for various cancers including breast cancer, Hodgkin's disease, Kaposi's sarcoma, and testicular cancer. The vinca alkaloids are structurally similar compounds comprised of 2 multiringed units, vindoline and catharanthine. The vinca alkaloids have become clinically useful since the discovery of their antitumour properties in 1959. Initially, extracts of the periwinkle plant (Catharanthus roseus) were investigated because of putative hypoglycemic properties, but were noted to cause marrow suppression in rats and antileukemic effects in vitro. Vincristine binds to the microtubular proteins of the mitotic spindle, leading to crystallization of the microtubule and mitotic arrest or cell death. Vincristine has some immunosuppressant effect. The vinca alkaloids are considered to be cell cycle phase-specific.

Toxicity

IVN-RAT LD₅₀ 1300 mg/kg; IPR-MUS LD₅₀ 5.2 mg/kg

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Half Life

19-155 hours

Protein Binding

~75%

References

• Graf WD, Chance PF, Lensch MW, Eng LJ, Lipe HP, Bird TD: Severe vincristine neuropathy in Charcot-Marie-Tooth disease type 1A. Cancer. 1996 Apr 1;77(7):1356-62. [Pubmed]

• Qweider M, Gilsbach JM, Rohde V: Inadvertent intrathecal vincristine administration: a neurosurgical emergency. Case report. J Neurosurg Spine. 2007 Mar;6(3):280-3. [Pubmed]

• JOHNSON IS, ARMSTRONG JG, GORMAN M, BURNETT JP Jr: THE VINCA ALKALOIDS: A NEW CLASS OF ONCOLYTIC AGENTS. Cancer Res. 1963 Sep;23:1390-427. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Wikipedia

Vincristine

Molecule Details

References

PubChem Literature

From Data Sources

• Graf WD, Chance PF, Lensch MW, Eng LJ, Lipe HP, Bird TD: Severe vincristine neuropathy in Charcot-Marie-Tooth disease type 1A. Cancer. 1996 Apr 1;77(7):1356-62. Pubmed

• JOHNSON IS, ARMSTRONG JG, GORMAN M, BURNETT JP Jr: THE VINCA ALKALOIDS: A NEW CLASS OF ONCOLYTIC AGENTS. Cancer Res. 1963 Sep;23:1390-427. Pubmed

• Qweider M, Gilsbach JM, Rohde V: Inadvertent intrathecal vincristine administration: a neurosurgical emergency. Case report. J Neurosurg Spine. 2007 Mar;6(3):280-3. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Names and Identifiers

Synonyms

vincristineVincristina [DCIT]Vincristinum [INN-Latin]VCRLeurocristineVincrystineVincristine22-OxovincaleukoblastineVINLCRIndole alkaloidZ-D-Val-Lys(Z)-OHVincristine SulfateVincrstine

Brand Name

VincrexVincristine Sulfate PFSOncovinVincasarVinkristinMarqiboVincasar PFSOnco TCS

IUPAC name

IUPAC Traditional name

sulfate, vincristine vincristine sulfate

Registration numbers

PubChem SID

PubChem CID

CAS Number

Medline Plus

CHEBI ID

Wikipedia Title

Unique Ingredient Identifier

CHEMBL

KEGG ID

DrugBank ID

Chemspider ID

ATC CODE

Molecule Details

DB00541

Drug Groups

approved; investigational

Description

Antitumor alkaloid isolated from Vinca Rosea. (Merck, 11th ed.)

Indication

For treatment of acute leukaemia, malignant lymphoma, Hodgkin's disease, acute erythraemia, acute panmyelosis

Pharmacology

Toxicity

IVN-RAT LD₅₀ 1300 mg/kg; IPR-MUS LD₅₀ 5.2 mg/kg

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Half Life

19-155 hours

Protein Binding

~75%

References

• Graf WD, Chance PF, Lensch MW, Eng LJ, Lipe HP, Bird TD: Severe vincristine neuropathy in Charcot-Marie-Tooth disease type 1A. Cancer. 1996 Apr 1;77(7):1356-62. [Pubmed]

• Qweider M, Gilsbach JM, Rohde V: Inadvertent intrathecal vincristine administration: a neurosurgical emergency. Case report. J Neurosurg Spine. 2007 Mar;6(3):280-3. [Pubmed]

• JOHNSON IS, ARMSTRONG JG, GORMAN M, BURNETT JP Jr: THE VINCA ALKALOIDS: A NEW CLASS OF ONCOLYTIC AGENTS. Cancer Res. 1963 Sep;23:1390-427. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Wikipedia

Vincristine

References

PubChem Literature

From Data Sources

• Graf WD, Chance PF, Lensch MW, Eng LJ, Lipe HP, Bird TD: Severe vincristine neuropathy in Charcot-Marie-Tooth disease type 1A. Cancer. 1996 Apr 1;77(7):1356-62. Pubmed

• JOHNSON IS, ARMSTRONG JG, GORMAN M, BURNETT JP Jr: THE VINCA ALKALOIDS: A NEW CLASS OF ONCOLYTIC AGENTS. Cancer Res. 1963 Sep;23:1390-427. Pubmed

• Qweider M, Gilsbach JM, Rohde V: Inadvertent intrathecal vincristine administration: a neurosurgical emergency. Case report. J Neurosurg Spine. 2007 Mar;6(3):280-3. Pubmed

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

2.8

Molecule

ID:423